Methyl Acrylate → HCID 118023217, compound

HRID 514987Notes

Reaction equation

HRID 514987 reaction equation
Cl.Cl.[NH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[NH2:4].[C:11](OC)(=[O:14])[CH:12]=[CH2:13].C[O-].[Na+].[O-]CC.[Na+]>>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([N:3]2[CH2:13][CH2:12][C:11](=[O:14])[NH:4]2)[CH:6]=1

Participants

5

Reactant 4

HCID 7294Methyl AcrylateHCID 2723922Sodium ethoxideHCID 10942334Sodium MethoxideHCID 171324893-Hydrazinylpyridine dihydrochloride

Product 1

HCID 118023217HCID 118023217, compound

Procedure

In step a of Scheme 1, 3-hydrazinopyridine dihydrochloride is reacted with methyl acrylate in the presence of a base such as sodium methoxide or sodium ethoxide to yield 1-(pyridin-3-yl)pyrazolidin-3-one followed by chlorination of 1-(pyridine-3-yl)pyrazolidin-3-one with phosphoryl chloride (POCl3) in a two-step process to yield dihydropyrazole chloride (5a). The first step may be conducted in a polar protic solvent such as, methanol (MeOH) or ethanol (EtOH), at a temperature from about 40° C. to about 80° C. The second step may be conducted neat in phosphoryl chloride at a temperature from about 40° C. to about 80° C. When the crude product from the first step was neutralized, the second step can also be conducted in a solvent like acetonitrile (MeCN) at a temperature from about 40° C. to about 80° C.

Sources & evidence

ORD record
ord-bc14cbafa56d42b292513f201572c10c
Source dataset
uspto-grants-2015_08
Patent number
US09108946B2

Reaction notes

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